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New Canaan vacation rentals

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Scroll through and select from vacation rentals in New Canaan to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a pool. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - New Canaan

Showing deals for:Aug 14 - Aug 21

Image gallery for Darien family home on a Cul de Sac with pond.

Exterior
9.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
Price is $819
$5,733 for 7 nights
All fees included
Darien family home on a Cul de Sac with pond.

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Find out more about New Canaan

Why visit New Canaan

  • Scenic Nature Preserves: Explore beautiful parks and nature preserves, perfect for hiking, picnicking, and enjoying the outdoors.
  • Charming City Center: Stroll through the picturesque downtown, featuring unique shops, restaurants, and local art galleries.
  • Architectural Marvels: Admire stunning homes and architecture that reflect New England’s rich design heritage.
  • Family-Friendly Activities: Enjoy a variety of attractions suitable for families, ensuring fun for all ages.
  • Cozy Accommodations: Choose from a range of vacation rentals, from charming cottages to comfortable apartments.

Popular types of accommodation in New Canaan

Discover the charm of New Canaan with a variety of vacation rentals to suit your needs. Whether you're seeking houses, cozy cottages, or comfortable apartments, our platform offers a selection of home rentals in New Canaan, CT. Explore rental listings that provide the perfect backdrop for your getaway, ensuring you find the ideal accommodation for your stay. Let your adventure begin in this picturesque town.

  • Houses: The top choice for rentals in New Canaan, ideal for families or groups seeking comfort and privacy.
  • Apartments: A popular option for travelers looking for convenience and amenities in a more compact space.
  • Cottages: Charming and cozy, these rentals offer a quaint retreat with a homey feel.
  • Cabins: Perfect for those wanting a rustic experience, often nestled in nature.
  • Condos: A great blend of space and luxury, these units provide modern living in a community setting.**

Top attractions in and around New Canaan

New Canaan, Connecticut, is perfect for outdoor family vacations or urban adventures. Visitors can explore a variety of attractions, including urban parks, nature preserves, and nearby beaches. Whether you're seeking a cultural experience or just some fun in the sun, New Canaan offers a range of activities that cater to all interests, making it an ideal destination for families and travelers alike.

  • The Glass House: A stunning architectural masterpiece and museum designed by Philip Johnson, The Glass House showcases modernist design and offers a serene environment surrounded by beautiful gardens and landscapes, enhancing its cultural vibe.
  • Historic South Norwalk: Located only 5 miles away, this charming district features preserved 19th-century architecture, unique shops, and waterfront dining, immersing visitors in the rich history and culture of the area.
  • Stamford Museum and Nature Center: Situated 3 miles from New Canaan, this environmental center combines art, nature, and education, featuring exhibits, nature trails, and a focus on eco-friendly initiatives, making it a perfect spot for families and nature enthusiasts.

Things to do recommended for couples

For a romantic getaway in New Canaan, enjoy a concert at Levitt Pavilion for vibrant entertainment, unwind with a soothing treatment at Hand & Stone Massage and Facial Spa, or indulge in luxury at the Greenwich Polo Club. Each experience promises memorable moments for couples.

Things to do recommended for families

Families visiting New Canaan can enjoy exciting activities at Chelsea Piers, just a short drive away for sports enthusiasts. Waveny Park offers a serene retreat for relaxation, while the Rolnick Observatory provides entertaining family experiences with its captivating planetarium shows.

Things to do recommended for groups

Groups visiting New Canaan can enjoy shopping and entertainment at Stamford Town Center and Springdale Shopping Center, both offering vibrant atmospheres. For a cultural experience, catch a performance at the Stamford Center for the Arts, perfect for family and romantic outings.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in New Canaan

If you're traveling with a group, family, or pets, or if you're considering an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to New Canaan with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to New Canaan with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to New Canaan: For many families, a trip isn't truly complete without their furry companion by their side. If you can relate to this, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting New Canaan: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near New Canaan

New Canaan, Connecticut, offers a delightful blend of outdoor activities, family-friendly attractions, and charming city vibes. Explore the picturesque city center, admire the stunning New Canaan homes, and discover the essence of a quintessential New England town. Nearby areas provide a rich atmosphere filled with history and friendly locals, making it an ideal destination for a romantic getaway or a fun family vacation.

  • Stamford: Located 7 miles away from New Canaan, Stamford is a vibrant city known for its diverse activities catering to families and outdoor enthusiasts. Visitors can enjoy a dynamic shopping scene, catch a show at one of the theaters, or engage in educational experiences. Popular attractions include the bustling tourist precinct and the modern square, where you can explore local dining and entertainment options. Stamford's blend of urban life and outdoor spaces makes it an ideal destination for a family outing or a leisurely day of exploration.
  • Norwalk: Just 5 miles from New Canaan, Norwalk offers a delightful mix of family-friendly activities and outdoor adventures. The city is home to beautiful beaches where families can relax and enjoy the sun, as well as historic sites that provide a glimpse into the area's rich past. Norwalk also boasts a variety of shopping areas and educational venues for all ages. Whether you’re looking to spend a day at the beach or explore charming historic locations, Norwalk promises a memorable experience for visitors.
  • Westport: Situated 7 miles from New Canaan, Westport is a picturesque city perfect for outdoor enthusiasts and families alike. With its stunning beaches, serene lakes, and recreational areas, Westport is an excellent spot for outdoor activities, picnics, and nature walks. The city also features a vibrant arts scene with theaters offering various performances. For couples seeking a romantic getaway, the scenic waterfront and quaint downtown area provide a charming backdrop for memorable moments together. Westport is truly a gem worth exploring.

Best time to go to New Canaan

If you're planning a trip to New Canaan, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like February, October and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.7°F (-0.7°C)Light RainMostly SunnyAverageSlightly Low
February32.0°F (0.0°C)Light RainMostly SunnySlightly LowSlightly Low
March38.7°F (3.7°C)Light RainMostly SunnyAverageSlightly Low
April48.9°F (9.4°C)Light RainMostly SunnySlightly HighAverage
May59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
June67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
July74.7°F (23.7°C)Light RainMostly SunnySlightly HighSlightly High
August73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
September66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
October56.7°F (13.7°C)Light RainMostly SunnySlightly LowAverage
November45.1°F (7.3°C)Light RainMostly SunnyAverageAverage
December37.2°F (2.9°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy even greater savings. To discover a Vrbo property that suits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily view and organize your travel plans. Any properties you've saved or booked are now categorized under Potential, Upcoming, or Current Trips for your convenience. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the oceanfront landscape of New Canaan

Experience the unique character of New Canaan with a stay in a vacation home rental. This romantic city allures visitors with its coral reefs and seafood restaurants. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around New Canaan

Are you looking for attractions to see in the area? Venture out of your cozy vacation rental and experience everything that New Canaan has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Norwalk Maritime Aquarium (5.2 mi / 8.4 km)
  • Hand & Stone Massage and Facial Spa (6.1 mi / 9.8 km)
  • Chelsea Piers (6.6 mi / 10.6 km)
  • Rye Playland (15.6 mi / 25.1 km)
  • Beardsley Zoo (16.9 mi / 27.2 km)
  • Bayville Adventure Park (17.1 mi / 27.6 km)

Exploring the natural landscape of New Canaan

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, New Canaan is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Pound Ridge Town Park (5.4 mi / 8.7 km)
  • Old Mill Beach (6.3 mi / 10.2 km)
  • Calf Pasture Beach (6.8 mi / 10.9 km)
  • Cove Island Park (6.9 mi / 11.1 km)
  • Houston Preserve (6.9 mi / 11.2 km)
  • Cummings Park Beach (7.5 mi / 12.1 km)

Transportation options to and around New Canaan

Fly into Westchester County Airport (HPN), the closest airport, located 12.1 mi (19.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 15.6 mi (25.1 km) away.

Frequently asked questions

What is the best area to stay in New Canaan, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in New Canaan, Connecticut, a popular area to stay is near the downtown district. This vibrant neighborhood offers a charming small-town atmosphere, with a delightful array of boutiques, cafes, and restaurants. Visitors can enjoy easy access to top attractions such as the New Canaan Nature Center, which features beautiful trails and educational programs, and the iconic Philip Johnson Glass House, a masterpiece of modern architecture that attracts design enthusiasts.

Another excellent option is the area surrounding Waveny Park, a picturesque green space that is great for outdoor activities. The park features walking trails, sports facilities, and a stunning mansion that hosts various community events. Staying in this neighborhood provides a peaceful retreat while still being close to the heart of New Canaan's cultural offerings.
How much does it cost to rent a vacation home in New Canaan?
Prices for vacation rentals in New Canaan vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in New Canaan to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for New Canaan vacation house rentals?
You can find great discounts on house rentals in New Canaan on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in New Canaan?
In New Canaan, vacation houses are a popular choice, with several available throughout the area. These properties typically feature spacious layouts ideal for families or groups, including multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Additionally, several apartments and villas can be found, offering a more compact yet comfortable stay, often equipped with modern amenities like Wi-Fi and laundry facilities. Cottages are also available, providing a quaint, homey atmosphere for travelers seeking a charming escape.
Are there any family house rentals in New Canaan?
In New Canaan, Connecticut, there are several family-friendly house rentals available, making it a great choice for those traveling with children. The town features spacious homes that often come with multiple bedrooms, allowing for comfortable accommodations for larger families. Many of these properties include amenities such as full kitchens, where families can prepare meals together, and outdoor spaces that may have patios or gardens for kids to enjoy.

Located in close proximity to local parks and recreational areas, visitors can take advantage of nearby playgrounds and open spaces for outdoor activities. The charming downtown area offers shops and cafes, providing opportunities for family outings.
Can I rent a vacation home with a pool or hot tub in New Canaan?
In New Canaan, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and luxury. This charming town is known for its picturesque neighborhoods and beautiful landscapes, ideal for enjoying outdoor amenities. Many of these rentals come equipped with private pools, spacious outdoor areas, and hot tubs, providing a ideal setting for unwinding after a day of exploring.
Can I find long-stay vacation rentals in New Canaan?
A long-stay vacation rental in New Canaan is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in New Canaan?
In New Canaan, there are several pet-friendly house rentals available, providing a comfortable stay for travelers with pets. Many of these vacation homes are situated in charming neighborhoods that offer a blend of suburban tranquility and easy access to local parks and outdoor spaces. Expect amenities such as spacious backyards, modern kitchens, and cozy living areas, making these rentals ideal for families or groups.

The town is home to several parks, including Waveny Park, which features walking trails, open fields, and picnic areas, superb for enjoying time outdoors with your furry friends. Additionally, the nearby Mead Park offers more recreational opportunities with its playgrounds and sports facilities.
Are there any remote work vacation rentals in New Canaan?
In New Canaan, Connecticut, there are several remote work vacation rentals available that cater to travelers needing a productive environment. Many of these properties are equipped with essential amenities such as high-speed internet and Wi-Fi, ensuring a reliable connection for remote work. You'll often find dedicated workspaces, including desks and comfortable chairs, allowing for a conducive working atmosphere.

The town itself is known for its charming residential feel and proximity to beautiful parks, which can provide a nice break during work hours. New Canaan also offers a variety of local shops and dining options, making it convenient for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any New Canaan vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in New Canaan with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in New Canaan?
In New Canaan, popular rental amenities cater to travelers seeking comfort and convenience. Many properties come equipped with kitchens, allowing guests to prepare their own meals. Additionally, amenities such as blenders are often included for those who enjoy smoothies or quick snacks. Outdoor spaces like decks or patios are common, providing a nice area to relax and enjoy the surrounding scenery. For added warmth and ambiance, fireplaces are featured in various rentals, making them inviting during colder months. Furthermore, many accommodations are pet-friendly, allowing travelers to bring their furry companions along for the stay.
When is the best time to visit New Canaan for a vacation rental?
The best time to visit New Canaan for a vacation rental is during the peak season from April to June. This period attracts travelers looking to enjoy the vibrant spring atmosphere as the gardens bloom and outdoor activities abound. Visitors can take leisurely strolls through the picturesque town and explore the beautifully maintained parks, making it ideal for sightseeing and enjoying the pleasant weather.

April, in particular, is a delightful month to experience New Canaan. Temperatures generally range from the mid-40s to mid-60s Fahrenheit, providing a comfortable climate for outdoor adventures such as hiking in nearby nature reserves or visiting local art galleries. The community's charm shines through with various events and festivals celebrating the season, ensuring there's always something engaging happening.

For those seeking budget-friendly options, consider visiting in December. While this month is quieter in terms of tourist activity, it offers a unique charm with holiday decorations and cozy indoor experiences, making it great for a peaceful getaway.
How early should I book a New Canaan vacation rental?
Book your New Canaan vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in New Canaan, Connecticut, United States of America?
In New Canaan, visitors can enjoy a variety of attractions that highlight the town's charm and natural beauty. The Waveny Park is a standout destination, featuring expansive lawns, beautiful gardens, and a historic mansion, making it a superb spot for picnics and leisurely walks. The New Canaan Nature Center offers trails and interactive exhibits, providing an engaging experience for families and nature enthusiasts alike.

For those interested in art and culture, the Philip Johnson Glass House is a must-visit. This architectural landmark showcases modern design and is surrounded by picturesque landscapes. The downtown area, with its quaint shops and local eateries, provides a delightful atmosphere for shopping and dining. Additionally, the New Canaan Historical Society offers insights into the town's rich history through various exhibits and events.
Can I change or cancel my New Canaan home rental booking on Vrbo?
To find New Canaan vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the New Canaan vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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